4-Methylpyridine → 1-(2-Furyl)-2-pyridin-4-ylethanone

HRID 353209

反応式

HRID 353209 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[N:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](OCC)=[O:24].CCCCCC>O1CCCC1>[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](=[O:24])[CH2:17][C:14]1[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=1

参加物

6

反応物 4

HCID 79634-MethylpyridineHCID 8058HexaneHCID 11980Ethyl 2-furoateHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 227080301-(2-Furyl)-2-pyridin-4-ylethanone収率 70.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In a nitrogen atmosphere, lithium bis (trimethylsilyl) amide (100 mL, 100 mmol) was added dropwise into a solution of 4-picoline (4.6 g, 49.4 mmol) and ethyl 2-furancarboxylate (7.7 g, 54.9 mmol) in tetrahydrofuran (40 mL) at 0° C. over 1 hour, followed by stirring as it was for 2 hours. Hexane (140 mL) was added to the reaction solution, and the resulting crystals were collected by filtration. The resulting crystals were dissolved in ethyl acetate and an aqueous saturated solution of ammonium chloride. The organic layer was washed with an aqueous saturated solution of ammonium chloride (×2) and brine, dried over anhydrous sodium sulfate, and concentrated. Hexane was added to the residue, and the resulting precipitates were collected by filtration and washed with hexane, to give the title compound (6.5 g, 70%) as a pale yellow solid.

後処理

  1. filtrationthe resulting crystals were collected by filtration
  2. dissolutionThe resulting crystals were dissolved in ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated solution of ammonium chloride (×2) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionHexane was added to the residue
  7. customthe resulting precipitates
  8. filtrationwere collected by filtration
  9. washwashed with hexane

出典と根拠

ORDレコード
ord-44405439bb6c4ba681347cc4241f19f9
出典データセット
uspto-grants-2004_06
特許番号
US06750232B2

関連ノート

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